T9823

Tetracycline hydrochloride

Biotechnology Performance Certified, suitable for cell culture, ≥95%

• Empirical Formula (Hill Notation): C₂₂H₂₄N₂O₈ · HCl
• CAS Number: 64-75-5
• Molecular Weight: 480.90
• Beilstein/REAXYS Number: 3844873
• EC Number: 200-593-8
• MDL number: MFCD00078142
• UNSPSC Code: 51101500
• PubChem Substance ID: 24900607

Properties

• grade: Biotechnology Performance Certified
• assay: ≥95%
• technique(s): cell culture | mammalian: suitable
• impurities: endotoxin, tested
• mp: 220-223 °C (lit.)
• solubility: H₂O: soluble 50 mg/mL
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive bacteria
• mode of action: protein synthesis | interferes
• storage temp.: −20°C
• SMILES string: Cl.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)cccc4[C@@]3(C)O
• InChI: 1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1
• InChI key: XMEVHPAGJVLHIG-FMZCEJRJSA-N

Description

General description

Chemical structure: tetracycline

Application

Tetracycline is a broad spectrum polyketide antibiotic. It is used clinically to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever and Brill-Zinsser disease. It is used to treat upper respiratory infections and acne. It is used to study multidrug resistance as well as potential side effects such as acute pancreatitis. It has been used in target and resistance based mechanistic studies of novel antibiotics.

Biochem/physiol Actions

Tetracycline inhibits bacterial protein synthesis elongation at the level of aminoacyl-tRNA binding to the 30S ribosome. Tetracycline passively diffuses through porin channels in the bacterial cell membrane. It also binds to the bacterial 50S ribosomal subunit which may alter the cytoplasmic membrane, causing intracellular components to leak from bacterial cells. Mode of resistance is loss of cell wall permeability.

Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.

Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.

Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.

Safety Information

• pictograms: GHS08,GHS07,GHS09
• signalword: Warning
• hcodes: H315,H319,H335,H361fd,H410
• pcodes: P202 - P261 - P273 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Aquatic Acute 1 - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves